Trifluoromethanesulfonic Anhydride

Trifluoromethanesulfonic anhydride
Names
	Preferred IUPAC name Trifluoromethanesulfonic anhydride
Identifiers
CAS Number	358-23-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48509;
ChemSpider	61068;
EC Number	206-616-8;
PubChem CID	67749;
UNII	8W034LHG1U ;
	InChI InChI=1S/C2F6O5S2/c3-1(4,5)14(9,10)13-15(11,12)2(6,7)8 Key: WJKHJLXJJJATHN-UHFFFAOYSA-N;
	SMILES C(F)(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F;
Properties
Chemical formula	C2F6O5S2
Molar mass	282.13 g·mol−1
Appearance	colourless liquid
Density	1.6770 g/mL
Boiling point	82 °C (180 °F; 355 K)
Solubility in water	Reacts to form Triflic acid
Hazards
Safety data sheet	Fisher MSDS
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H272, H302, H314, H335
NFPA 704 (fire diamond)	0 4 3 W; OX
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Trifluoromethanesulfonic anhydride, also known as triflic anhydride, is the chemical compound with the formula (CF₃SO₂)₂O. It is the acid anhydride derived from triflic acid. This compound is a strong electrophile, useful for introducing the triflyl group, CF₃SO₂. Abbreviated Tf₂O, triflic anhydride is the acid anhydride of the superacid triflic acid, CF₃SO₂OH.^[2]^[3]

Preparation and uses

Triflic anhydride is prepared by dehydration of triflic acid using P₄O₁₀.^[2]

Triflic anhydride is useful for converting ketones into enol triflates.^[4]

In a representative application, is used to convert an imine into a NTf group.^[5] It will convert phenols into a triflic ester, which enables cleavage of the C-O bond.^[6]^[7]

Assay

The typical impurity in triflic anhydride is triflic acid, which is also a colorless liquid. Samples of triflic anhydride can be assayed by ¹⁹F NMR spectroscopy: −72.6 ppm^[8] vs. −77.3 for TfOH (std CFCl₃).

Safety

It is an aggressive electrophile and readily hydrolyzes to the strong acid triflic acid. It is very harmful to skin and eyes.^[9]

References

↑ Bloodworth, A.J.; Curtis, Richard J.; Spencer, Michael D.; Tallant, Neil A. (March 1993). "Oxymetallation. Part 24. Preparation of cyclic peroxides by cycloperoxymercuriation of unsaturated hydroperoxides.". Tetrahedron 49 (13): 2729–2750. doi:10.1016/S0040-4020(01)86350-X.
↑ ^2.0 ^2.1 Martínez, A. G.; Subramanian, L. R.; Hanack, M. (2016). "Trifluoromethanesulfonic Anhydride". Encyclopedia of Reagents for Organic Synthesis: 1–17. doi:10.1002/047084289X.rt247.pub3. ISBN 9780470842898.
↑ Baraznenok, Ivan L.; Nenajdenko, Valentine G.; Balenkova, Elizabeth S. (May 2000). "Chemical Transformations Induced by Triflic Anhydride". Tetrahedron 56 (20): 3077–3119. doi:10.1016/S0040-4020(00)00093-4.
↑ Cacchi, Sandro; Morera, Enrico; Ortar, Giorgio (2011). "Discussion Addendum for: Palladium-Catalyzed Reduction of Vinyl Trifluoromethanesulfonates to Alkenes: Cholesta-3,5-diene". Organic Syntheses 88: 260. doi:10.15227/orgsyn.088.0260.
↑ Baker, T. J.; Tomioka, M.; Goodman, M. (2002). "Preparation and Use of N,N'-Di-BOC-N''-Triflylguanidine". Organic Syntheses 78: 91. doi:10.15227/orgsyn.078.0091.
↑ McWilliams, J. C.; Fleitz, F. J.; Zheng, N.; Armstrong, III, J. D.. "Preparation of n-Butyl 4-Chlorophenyl Sulfide". Organic Syntheses 79: 43. doi:10.15227/orgsyn.079.0043.
↑ Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. (1999). "(R)-(+)- and (S)-(−)-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl (BINAP)". Organic Syntheses 76: 6. doi:10.15227/orgsyn.076.0006.
↑ Dell'Amico, Daniela Belli; Boschi, Daniele; Calderazzo, Fausto; Labella, Luca; Marchetti, Fabio (28 February 2002). "Synthesis, and crystal and molecular structures of the triflato and trifluoroacetato complexes of zinc, Zn(O3SCF3)2(DME)2 and [Zn(O2CCF3)2(DME)n"]. Inorganica Chimica Acta 330 (1): 149–154. doi:10.1016/S0020-1693(01)00739-3. http://144.206.159.178/ft/458/52133/914984.pdf.
↑ "MSDS - 176176". https://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=176176&brand=ALDRICH&PageToGoToURL=https://www.sigmaaldrich.com/catalog/product/aldrich/176176?lang=en.

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[1] Bloodworth, A.J.; Curtis, Richard J.; Spencer, Michael D.; Tallant, Neil A. (March 1993). "Oxymetallation. Part 24. Preparation of cyclic peroxides by cycloperoxymercuriation of unsaturated hydroperoxides.". Tetrahedron 49 (13): 2729–2750. doi:10.1016/S0040-4020(01)86350-X.

[eros-2] 2.0 ^2.1 Martínez, A. G.; Subramanian, L. R.; Hanack, M. (2016). "Trifluoromethanesulfonic Anhydride". Encyclopedia of Reagents for Organic Synthesis: 1–17. doi:10.1002/047084289X.rt247.pub3. ISBN 9780470842898.

[3] Baraznenok, Ivan L.; Nenajdenko, Valentine G.; Balenkova, Elizabeth S. (May 2000). "Chemical Transformations Induced by Triflic Anhydride". Tetrahedron 56 (20): 3077–3119. doi:10.1016/S0040-4020(00)00093-4.

[4] Cacchi, Sandro; Morera, Enrico; Ortar, Giorgio (2011). "Discussion Addendum for: Palladium-Catalyzed Reduction of Vinyl Trifluoromethanesulfonates to Alkenes: Cholesta-3,5-diene". Organic Syntheses 88: 260. doi:10.15227/orgsyn.088.0260.

[5] Baker, T. J.; Tomioka, M.; Goodman, M. (2002). "Preparation and Use of N,N'-Di-BOC-N''-Triflylguanidine". Organic Syntheses 78: 91. doi:10.15227/orgsyn.078.0091.

[6] McWilliams, J. C.; Fleitz, F. J.; Zheng, N.; Armstrong, III, J. D.. "Preparation of n-Butyl 4-Chlorophenyl Sulfide". Organic Syntheses 79: 43. doi:10.15227/orgsyn.079.0043.

[7] Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. (1999). "(R)-(+)- and (S)-(−)-2,2'-Bis(Diphenylphosphino)-1,1'-Binaphthyl (BINAP)". Organic Syntheses 76: 6. doi:10.15227/orgsyn.076.0006.

[Amico2002-8] Dell'Amico, Daniela Belli; Boschi, Daniele; Calderazzo, Fausto; Labella, Luca; Marchetti, Fabio (28 February 2002). "Synthesis, and crystal and molecular structures of the triflato and trifluoroacetato complexes of zinc, Zn(O3SCF3)2(DME)2 and [Zn(O2CCF3)2(DME)n"]. Inorganica Chimica Acta 330 (1): 149–154. doi:10.1016/S0020-1693(01)00739-3. http://144.206.159.178/ft/458/52133/914984.pdf.

[9] "MSDS - 176176". https://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=176176&brand=ALDRICH&PageToGoToURL=https://www.sigmaaldrich.com/catalog/product/aldrich/176176?lang=en.

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Trifluoromethanesulfonic Anhydride

Contents

Preparation and uses

Assay

Safety

See also

References